Annapolis Overlook Homes under $400,000

Annapolis Overlook Homes under $400,000

Welcome to Annapolis Overlook, a charming subdivision nestled in the heart of beautiful Annapolis, Maryland! This vibrant community perfectly blends suburban tranquility with the rich history and lively culture of one of the oldest cities in the United States. With its picturesque tree-lined streets and welcoming atmosphere, Annapolis Overlook is an ideal place for families, young professionals, and retirees alike.

One of the standout features of this delightful subdivision is the availability of homes priced under $400,000. This makes Annapolis Overlook an attractive option for first-time homebuyers or those looking to downsize without compromising on quality of life. The homes in this community often boast modern amenities, spacious layouts, and inviting outdoor spaces, perfect for enjoying the beautiful Maryland weather.

Living in Annapolis Overlook means you’re just a stone’s throw away from the rich maritime history and vibrant arts scene that Annapolis is famous for. Spend your weekends exploring the historic downtown area, where you can visit the U.S. Naval Academy, indulge in local cuisine at charming restaurants, or stroll along the scenic waterfront. Additionally, residents enjoy easy access to major highways, making commuting a breeze.

Whether you’re looking for a cozy starter home or a charming retreat, Annapolis Overlook offers a unique opportunity to experience the best of Annapolis living at an affordable price. Don’t miss your chance to become part of this welcoming community—your dream home awaits!

Newest Annapolis Overlook Homes under $400,000

30 Hearthstone Ct Unit G, Annapolis
$299,000
2 Beds ⋅ 2 Baths
Welcome home to this beautiful 2-bedroom, 2-bath home—the largest model in Annapolis Overlook! This bright spacious residence features an open concept layout, high ceilings, crown molding, abundant natural light, and a cozy two-sided wood-burning fireplace. The show stopping remodeled kitchen is designed for cooking and entertaining, featuring a stunning 6 foot quartz island, open shelving, ample cabinetry and storage, and generous workspace. It flows seamlessly into the oversized dining and living areas, creating the perfect gathering space. The primary suite offers high ceilings, plush carpeting, a walk-in closet with a professional organizer, and an en suite bath with a soaking tub. The second bedroom is filled with natural light and includes its own full en suite bath. Enjoy peaceful wooded views from your private balcony, plus an in-home washer and dryer and ample storage throughout. Community amenities include a pool, fitness center, two assigned parking spaces, exterior maintenance, lawn care, trash, and snow removal. Conveniently located just minutes from Downtown Annapolis, Quiet Waters Park, shopping, and major commuter routes. This is a must see property! Schedule your tour today!

30 Hearthstone Ct Unit G, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

40 Ironstone Ct Unit B, Annapolis
$335,000
3 Beds ⋅ 3 Baths
Nestled in the charming and convenient Annapolis Overlook community, this inviting townhouse offers a perfect blend of comfort and investment potential. This traditional-style townhome boasts 1,694 square feet of thoughtfully designed living space, making it an ideal choice for both homeowners and savvy investors looking to capitalize on a desirable rental market. Step inside to discover a warm, welcoming interior with an open floor plan that seamlessly connects the kitchen and dining areas. Brand-new luxury vinyl plank flooring highlights the combined living, kitchen, and dining spaces, making it perfect for entertaining with a touch of modern elegance. The kitchen also offers ample table space, making it a cozy spot for casual meals. The home features three spacious bedrooms, including a primary suite that encompasses the entire third floor, with a luxurious walk-in closet and an en-suite bathroom. Additional highlights include a laundry room, a second-floor bathroom, updated lighting, ceiling fans for added comfort, and plush carpeting that enhances the inviting atmosphere throughout. The stainless steel refrigerator and gas range, washer, dryer, carpet, and heat pump have all been updated within the past 5 years. The home has a brand-new storm door and bay window at the front of the house). Homeowners and investors will appreciate the low-maintenance lifestyle this property offers, with an association fee that includes lawn maintenance and snow removal. The community amenities include outdoor common grounds, a refreshing pool, and a fitness center. Parking is hassle-free with two parking permits included -one parking place is assigned and located directly in front of the townhome. An additional car can be parked (with permit), in the "Permit Required" spaces. The community's prime location (close proximity to Quiet Waters Park, Downtown Annapolis, the US Naval Academy, and shopping) ensures easy access to local amenities and attractions. Whether you're looking to buy or invest, this Annapolis Overlook property is a fantastic opportunity. With its blend of modern features, community amenities, and strategic location, it stands ready to deliver both comfort and value for years to come. Don't miss your chance to purchase this delightful home!

40 Ironstone Ct Unit B, Annapolis

Listing courtesy of RE/MAX One. Contact:

11 Winslow Ct, Annapolis
$315,000
2 Beds ⋅ 2 Baths
Tucked on a quiet court in The Landings, this move-in-ready 2-bedroom, 1.5-bath Annapolis townhome pairs easy living with rare, wooded privacy. It's about a 5-minute stroll to Truxtun Park for tennis, ball fields, trails, boat ramp and pool along Spa Creek, with Historic Downtown Annapolis, City Dock and the U.S. Naval Academy about 10 minutes away and Quiet Waters Park a short drive south. Inside, a bright white kitchen offers a butcher-block island, generous cabinetry, recessed lighting and a sunny window over the sink, flowing to a hardwood-floored living and dining area with a sliding door to the patio. Upstairs, two bedrooms showcase vaulted wood-plank ceilings, ceiling fans and ample closets. Out back, a covered paver patio, fully fenced yard and lush shade gardens create a private outdoor escape. Built in 1980 with community pool and tennis and quick access to Bay Ridge Ave, Forest Dr and Rt 50. Commute times are as follows (estimated): Minutes from the water in the Annapolis Neck/Eastport area of Anne Arundel County. About a 5-minute stroll to Truxtun Park for tennis, ball fields, trails, boat ramp, pool and Spa Creek access; roughly 10 minutes to Historic Downtown Annapolis, City Dock and the U.S. Naval Academy; about 7 minutes to Anne Arundel Medical Center; shopping within 1.3 miles; Quiet Waters Park and the Chesapeake Bay a short drive; fast Route 50, Bay Ridge Ave and Forest Dr access to Annapolis, Baltimore and D.C. Schedule a tour today!

11 Winslow Ct, Annapolis

Listing courtesy of Kelly and Co Realty, LLC. Contact:

50 Sandstone Ct Unit G, Annapolis
$280,000
2 Beds ⋅ 2 Baths
Welcome to 50-G Sandstone Court, nestled in the desirable Annapolis Overlook community, where comfort, convenience, and easy living come together. This beautifully maintained 2-bedroom, 2-bath condominium is truly move-in ready and offers a bright, welcoming atmosphere you'll be proud to call home. Step inside to discover a spacious, open-concept living area that creates the perfect setting for relaxing after a long day or gathering with family and friends. Natural light fills the space, while sliding glass doors lead to a private deck overlooking peaceful green space—an ideal spot to enjoy your morning coffee, unwind with a good book, or simply take in the outdoors. The thoughtfully designed kitchen features generous counter space, making meal preparation both convenient and enjoyable. Just off the kitchen, the adjoining dining area provides the perfect setting for everyday meals or entertaining guests. The tranquil primary suite is filled with natural light and offers serene views of the landscaped green space behind the building. An en-suite bath with a tub/shower combination provides both comfort and privacy. The second bedroom is generously sized with wall-to-wall carpeting and a spacious closet, making it ideal for guests, a home office, or additional living space. A second full bathroom with a tub/shower combination is conveniently located nearby. Whether you're a first-time homebuyer, looking to downsize, or seeking a low-maintenance lifestyle, this home offers the perfect combination of space, functionality, and location. Situated just minutes from Historic Downtown Annapolis, you'll enjoy easy access to charming boutiques, waterfront dining, marinas, entertainment, and the U.S. Naval Academy. Major commuter routes, shopping centers, parks, and everyday conveniences are all within close reach, making travel to Baltimore, Washington, D.C., and surrounding areas a breeze. Don't miss the opportunity to own this inviting home in a wonderful community—50-G Sandstone Court is ready to welcome you home.

50 Sandstone Ct Unit G, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

10 Sandstone Ct Unit K, Annapolis
$275,000
2 Beds ⋅ 2 Baths
PRICE REDUCED FOR QUICK SALE! Please reach out to CO-List Agent with any and all inquires including calls, texts, emails and offers. Back on the market with new photos! Welcome to this beautifully updated terrace-level condo offering the perfect blend of comfort and style. This 2-bedroom unit features fresh paint, brand-new carpet, and an upgraded kitchen complete with new countertops and stainless steel appliances. Enjoy easy single-level living with a spacious, open-concept layout that flows seamlessly to a private setting with peaceful forest views—ideal for relaxing or entertaining. Community amenities include an outdoor pool, fitness center, and clubhouse. Two reserved parking spaces convey. Now vacant, move-in ready, and one of the best updated values in the community—don't miss it! Now offered at a new, improved price, this move-in ready home is one of the best updated values in the community—don't miss it!

10 Sandstone Ct Unit K, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact:

40 Ironstone Ct Unit J, Annapolis
$329,000
3 Beds ⋅ 3 Baths
Beautifully maintained 3-level townhome in the desirable Annapolis Overlook community in Annapolis! This spacious home offers approximately 1,680 sq ft with 3 bedrooms, 2.5 baths, and a functional layout designed for comfortable living. The main level features a bright living area, separate dining space, and an updated kitchen with ample cabinet storage and room for entertaining. Upstairs you’ll find generously sized bedrooms including a primary suite with private bath and great closet space. Enjoy low-maintenance living in a well-established community conveniently located near downtown Annapolis, the Naval Academy, shopping, restaurants, and major commuter routes. The 21403 area is known for its coastal lifestyle, outdoor recreation, and close proximity to the Chesapeake Bay. Perfect for first-time buyers, investors, or anyone looking for easy living in a prime Annapolis location!

40 Ironstone Ct Unit J, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

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